


The First of Three Conversations

by Annakovsky



Category: New Girl
Genre: Anal Fingering, F/M, Flash Fic, M/M, Multi, Pegging, Strap-Ons, platonic sex helper
Language: English
Status: Completed
Published: 2014-09-20
Updated: 2014-09-20
Packaged: 2018-02-18 02:02:39
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,924
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2331125
Author URL: https://archiveofourown.org/users/Annakovsky/pseuds/Annakovsky
Summary: <blockquote class="userstuff">
              <p>Jess isn't entirely sure how Schmidt ended up here in her bedroom with them ("in an advisory capacity," Schmidt had said when this idea got brought up), sitting on the side of the bed next to a thing of lube and, uh, a strap-on. </p>
<p>(For accuracy: Mostly Nick/Jess, with background Nick/Schmidt.)</p>
            </blockquote>





	The First of Three Conversations

**Author's Note:**

> This is for the FIVE FICS FIVE DAYS challenge that Kyra and I are doing, so it was written all in one day for the bingo square "pegging."

Jess isn't entirely sure how Schmidt ended up here in her bedroom with them ("in an advisory capacity," Schmidt had said when this idea got brought up), sitting on the side of the bed next to a thing of lube and, uh, a strap-on. "I call this the introductory model," Schmidt says as he sets the strap-on down, crossing his legs casually like all of this is totally normal, like every friend gives his friends naked sex advice. "Oh, don't worry, Nicholas, I washed it," he says, before either Nick or Jess say anything at all.

Nick's eyes widen a little as he looks at the strap-on -- understandably, because frankly Jess thinks it looks a little bigger than it needs to for an introductory model. When Nick looks at her like he's thinking the same, for a second Jess thinks he's going to call this whole thing off. But then he swallows and rolls over onto his stomach, his whole bare back stretched out pale and vulnerable in front of her, his ass white and curved, and oh God, this is actually going to happen.

"All right, Jessica," Schmidt says, in the exact tone of voice he uses to instruct her on the correct temperature at which to store brie, half enjoying being imperious and half verging on outraged that she doesn't know this already. "A successful exercise in enjoyable anal intercourse lives and dies by one simple principle: prep work."

"Oh my God," Nick says, putting his hand up over his eyes, and Jess isn't sure if it's over the choice of words, the fact that Schmidt is here with them, or the fact that they're doing this at all. All three are a little alarming if she's being honest.

But she tries to focus up -- Nick wanted to do this, and she's going to do a good job at it if it kills her. Not like last time, trying to do the Captain, where Nick ended up limping around for two days afterwards. And since Schmidt and Cece were apparently experts in this particular area of sexual activity, Jess decided to ask Schmidt for advice, which is a decision she stands by even though it has clearly gotten pretty out of hand. "Okay," she says. She picks up the lube uncertainly. "Um, so… do I, uh, with my fingers, or…?"

"You have something else you want to prepare him with?" Schmidt says, laughing a little like he can't believe how dumb and sexually inexperienced Jess and Nick are. "Your big toe, perhaps?"

"Shut up, Schmidt," Jess says, and starts slicking her fingers up obediently, feeling like she's getting it all over the place, way too aware of Schmidt watching her like he thinks he could do this so much better.

Nick shifts around, squirming like he wants to look at them to see what's happening, but also Jess can tell he's working really hard not to look at Schmidt, which puts him in a bit of a pickle. "Okay, uh, I'll start out slow, 'kay, Nick?" she says, wanting to narrate for him a little bit so he knows what's going on without having to look around. 

"Yeah," Nick says, kind of low and embarrassed, and Jess starts sliding her slick fingers down his crack, trying to be soothing and gentle and not make any sudden movements. Nick squirms around a little more as she finally traces the outside of his hole, but it's less his embarrassed, nervous squirming, and more his turned-on squirming, so, uh -- well, that must be good, right? When Jess glances at Schmidt for some reassurance, he's totally staring with his eyes dark and his mouth a little bit open, and Jess looks away fast before she has to process much of whatever that is.

When Jess pushes her first finger inside, it sliding in easier than she expected since she used so much more lube this time than last time, Nick makes this little noise, and she immediately stops with her finger just barely inside him. "You okay?" she says, worried she hurt him, but his hips just move a little, pressing his ass up onto her finger in a way that surprises her.

"Yeah, yeah, I'm fine," he says, impatient in that way he gets when he's embarrassed he's into something, and oh. That was a hot noise. Huh.

Now Schmidt is shifting next to her, and Jess is afraid to look to see if that's uncomfortable-shifting or turned-on-shifting, because Nick and Schmidt have their whole, like, life-partners thing going on that she has always tried not to examine too closely, and she really does not want to know. She tries to focus in on Nick's ass, pressing her finger in further, listening to see if Nick makes that noise again. He does. It's kind of a _really_ hot noise.

"All right," Schmidt says once her finger's all the way in, clearing his throat a little, his voice raspy. "So now you want to find his prostate."

"His prostate?" Jess says. "Why?"

"Jessica Day!" Schmidt says, outraged. "Are you serious right now?! No wonder this went so badly the last time."

"Uh, it didn't go that badly," Jess says. 

"I beg to differ," Schmidt says. "I almost got you two to break up over that."

"Um, no, you didn't," Jess says. 

"Yes, I did," Schmidt says, talking over her. "I most certainly did, and --"

"-- and anyway, this part can't have been that bad, because Nick wanted to do it again," Jess says, talking over him right back.

"Um, guys?" Nick says. "Could you, uh -- move this along?"

Whoops. Jess has been kind of just keeping her finger there without moving it. "Sorry, Nick," she says, and tries to move her finger in a sexy way, pulling out, and then pressing back in again, not moving too hard in case she hurts him. And, uh, apparently looking for his prostate, for some reason?

"Okay," Schmidt says. "His prostate should be a couple of inches in, curl your finger up towards his front."

Jess does what he says, feeling around vaguely for it. "Uh, why am I doing this?" she says.

"What is wrong with the American sexual education system," Schmidt says, rolling his eyes. "The prostate is the male G-spot. Did you never even read Cosmo?"

"Don't be so mean!" Jess says. "I was just asking!" Fine, so, that's what's supposed to feel good or whatever? Schmidt could've just said that. She feels around a little more, but she really has no idea what she's looking for, and that must be obvious, because after a second Schmidt makes a huffy noise.

"For heaven's sake," he says. "You're rooting around like a hog looking for truffles."

Then all of a sudden Schmidt's finger is right next to hers on Nick's ass, all slicked up, and pressing in beside hers before she even knows what's happening. "Here," he says, like he's going to show her.

Jess's eyes almost bug out, and Nick shifts a little. "Um…," he says. "Jess, please tell me that's your other finger."

"I --" Jess starts to stammer out, but then Schmidt presses her finger against this little bulge inside Nick and Nick moans louder than she's ever heard him moan in the whole time they've been sleeping together, his hips jerking against the mattress.

"Yeah, like that," Schmidt says, smirking like he's so pleased with himself. 

Wow, that -- Jess tries it again, and Nick moans just as loud, just about humping the mattress now. "That feels good?!" Jess asks him.

"Um," Nick says. "Um, yeah?" his voice is kind of high pitched, and their fingers are stretching him out -- he feels way looser now, and Jess can see how she didn't do enough of this the last time. Not to mention how she didn't make him make those moaning sounds at all.

She starts moving her finger inside him a little more, pressing into that spot every time she pushes in, and Schmidt moves his finger too, and they set up a rhythm, fingering Nick together, and Nick's making a lot of noise now. After not even that long, Nick manages to get out, "Okay, I, okay, I want, you can, I think I'm ready."

And, oh God, oh God, he wants her to put the strap-on on, this is really happening, she's going to be the man and he's going to be the lady. She stares at Schmidt, eyes wide, because surely Nick can't be ready already, probably they should just keep doing the fingering for a little while longer, like, two to three weeks, right, but Schmidt nods at her gravely, like a NASA scientist indicating to an astronaut that they're ready for lift-off.

"Okay," Jess says, her voice a little wobbly, and she and Schmidt work their fingers out again, and then, honestly, it's a good thing that Schmidt is there, because Jess is pretty sure that if she tried to put this strap-on on by herself, with all the little buckles and the straps and how hard it is to get it positioned, quite possibly she would've ended up strangling herself, and it's not even supposed to go anywhere near her head.

The base of it has a little thing that actually goes a little ways inside her, and a part that rests against her clit, and she's already turned on enough from watching Nick go crazy getting fingered that she wants to moan just putting it on.

And then she's just… wearing a dick. There are her boobs and her hips and this black rubber dildo curving out from her crotch, such a weird thing to see, and Schmidt is rubbing lube all along it with an experienced hand. "Huh," she says, looking down at it, not even knowing how to feel about herself except, uh, kind of hot, actually.

Nick turns his head from one side to the other so now he can see her, and when he does his eyes widen. "Oh," he says faintly. While they've been putting this on, he got his knees under him, so Jess can kind of see how hard he is, his dick angry red and curved up against his stomach, and as he stares at her with his eyes wide his hand drifts towards it like he can't help himself.

"Yeah?" Jess says, starting to smile. She turns sideways so he can get a better look at it. Nick swallows visibly.

"Well, get over here, lady," he says, in this weak version of his funny, sexy gentleman voice. Like, how that funny, sexy gentleman would sound if he was too turned on to think straight.

Jess glances at Schmidt, just making sure that they're good to go here, and Schmidt is being weirdly subdued at this point, not even making any weird comments, kind of fading into the background. Staring at Nick a little, and then staring at Jess wearing this harness, but Jess is too distracted to worry too much about Schmidt at this point. 

"Okay, lovah," Jess says, in her funny, sexy lady voice, which is also a little feeble and breathy sounding to tell you the truth, and she moves up onto the bed behind Nick, starting to line the dildo up, her other hand on his hip. Her heart is pounding.

"Are we really doing this?" she says -- just, one last chance for them all to come back to their senses, right?

But: "Oh my God, Jess, hurry up," Nick says, and she starts to press inside.


End file.
